Learning Questions — How questions are the answer.

April 14, 2021
6 min read
“What’s the capital of Brazil?”
— Veronica Yan¹

How much are we actually understood? How much of the information we share is actually absorbed? How much is acted upon? How do we learn?

The “question” of “questions” came up as part of fassforward’s recent six-month study in remote learning. Interestingly, asking a question, even if the learner doesn’t know the answer, is probably a more effective way of learning — because questions focus attention. ²

The use of questions in the context of leadership, storytelling, and learning, is undervalued.

I’m telling you, there’s a problem.

Mid-size businesses lose nearly $500,000 a year due to misunderstandings. For larger businesses that number scales to an eye-watering $62.4 million a year.³ If we take that number as a proxy for not being understood or not being clear, we can see that as leaders, getting our message across is a challenge.

So what’s going wrong? Obviously, we’re not telling people what to do in a way that’s clear enough and loud enough. Maybe though, it’s the verb that’s the problem — ‘telling.’

Ask yourself how much of your day do you spend telling versus asking?

Why do questions provide the answer?

Questions are powerful. Not only do they reveal information — they come with a battery of positive side effects.

Are humans egocentric? The short answer is ‘yes’. We enjoy talking about ourselves. Self-disclosure brings pleasure. That pleasure transfers itself to the person who provoked it — namely the questioner. There’s a strong causal link between the number of questions someone asks and how likable they appear.⁴

Do people’s perspectives blind them? The short answer is yes. Questions build relevance. They lead someone to share their perspective. This helps you frame information within that person’s worldview. Questions jump-start conversations that might otherwise risk being polarized.⁵

Are people easily distracted? Yes. We’re good at thinking of one thing at a time. We’re bad at multitasking. When you ask someone a question, you hijack their brain. The process is known as instinctive elaboration.⁶ Getting someone to answer a question grabs their full attention.

Do questions help learning? Yes. They build self-reliance. The old saying “Give a man a fish, and he’ll eat for a day, teach a man to fish, and he’ll eat for a lifetime” comes into play here. Give someone the answer, and they’ll (probably) be OK for the moment. Guide them to think for themselves and they’ll self-learn for a lifetime.

This art of asking questions though is something many leaders, and many teachers, fail to practice.⁷

Why don’t we use questions more?

There are many reasons. As humans, we love speaking about ourselves. We are all our own favorite topic. Talking about someone else doesn’t always come naturally. For evidence, one has only to look at social media.

We’re eager to share our own opinions, and reach for ‘tell’ more readily than ‘ask.’

We’ve also spent 100 years being conditioned not to ask questions. “Curiosity killed the cat.” Victorian etiquette experts even discouraged asking questions.⁸ The echoes of that advice are still present today.

It might seem ludicrous, but those Victorian experts were actually on to something. They were sensing a fundamental awkwardness.  

Do questions make you nervous?

When humans communicate, two activities are happening. One is “impression management”⁹ — seeking to give the other person as positive a view of us as possible. The other is “information exchange” —  uncovering pieces of information that can help us.

Basically, we want people to like us, and find out what they know. Questions could help, but we tend not to use them. Our biases come roaring into action and make us tell, not ask.

Are you good at estimating? No.¹⁰ This is a fundamental failing of the human species. We overestimate people’s sensitivity to questions and underestimate their willingness to answer.

In negotiations or sales, for example, questions that would have been valuable, don’t get asked because we’re afraid of offending.¹¹

This costs us the chance to make a connection. Remember — people like answering questions about themselves. It also has actual material costs when questions are omitted during negotiations.

Do you avoid seeking help?

How about questions that seek out someone’s opinion or ask them for their help? Again, we fail to make accurate predictions. We secretly fear that asking for help damages our “impression management” score. In the game of impression management, we fear we get negative points if it appears we don’t know the answer or can’t cope.

Research¹² shows the exact opposite. When we ask for help, people build a more positive impression of our abilities. This is due to showing someone you value their expertise.

We need to ask more questions and ask them fearlessly.

Can interrogative questions build ideas?

Some questions open up ideas, while others close them down. Negotiation coach, Jim Camp, is the author of the article The science of asking great questions.¹³ He recommends avoiding questions that open with a verb.

Questions that start with “Should…?” “Would…?” “Is…?” or “Can…?” put people on the spot. They suggest right or wrong answers, requiring a definitive “Yes” or “No.”

Opening with interrogatives leads to wider, more open conversation. Any good journalist will recognize these questions. They’re the classic “who…?”, “what…?”, “where…?”, “when…?”, and “how…?”

  • “Who might represent new markets for the product?”
  • “What initiatives would make us the employer of choice for great talent?”
  • “Where are the parts of the business that could offer the most growth?”
  • “When are moments that we work well together as a team?”
  • “How can we embrace ideas and be responsive to emerging trends?”

These are big-picture questions that encourage thought and innovation.

Missing from the list is “why..?” While it’s an interrogative, “why” has an unfortunate side effect. It can personalize and cause defensiveness. It makes people feel pressured to justify themselves. “Why” leads to premature judgement. “Why” narrows the conversation and closes the debate.

How can refining questions drive outcomes?

Helping your team build ideas is one way to use questions in leadership and learning. Another is to take those ideas and move them to outcomes.

Our instinct when someone delivers an idea is to react.¹⁴ Before considering questions, we agree or disagree. This sends a clear message — that there are right answers or wrong answers, and we have already decided which is which.

An alternative approach is to use a questioning strategy that explores new ideas.

Do you have a questioning strategy?

Before agreeing or disagreeing, take the team or individual through a questioning tour. These questions can be as brief or as lengthy as time allows or the proposal deserves.


First, explore the foundation of the idea. If you understand the origin, then you’ll better grasp the context. Some possible questions to ask might be:

  • What started you down this path?
  • What’s the broader backstory for this?
  • Who already buys into this concept?
  • What’s the outcome you’re heading for?


From the foundation, move on to the path. These are questions that test assumptions and explore the chain of logic. Understand the logical components of the idea and how they link together. Look for assumptions and explore the evidence behind them. Be ready to constructively challenge any that appear flimsy.

  • How did you reach that conclusion?
  • Walk me through your reasoning.
  • What key assumptions is this based on?
  • What will break the chain of logic?


Our third stage encourages forward projection. If the proposal goes ahead, what are the likely consequences and impacts? Here’s where framing becomes important. Explore both the negative and the positive impacts — the pros and the cons. It’s easy at this stage for our own personal biases to flavor the questions. Ideas we like the sound of will receive positive questions, such as “How do you think this is going to help?” while ones we’re not so fond of receive the opposite.

  • If this happens, what else might happen as a result?
  • What could be the unintended consequences of this?
  • What are the positive impacts of this?
  • What are the negative impacts of this?


Everybody needs the service of a Devil’s Advocate from time to time. Anticipate counterarguments and look for any final flaws in the thinking. Consider rival ideas, alternative perspectives, or likely disagreements. Preparing for counterarguments is a great way to refine and strengthen your work.

  • What other perspectives need to be considered?
  • What disagreements might others put forward?
  • Which rival ideas might compete for attention?
  • What could go wrong?

Which persuades? Wind or warmth?

The Greek storyteller Aesop gave us the fable of  the Sun and the Wind. They had a bet to see who could get a traveller to remove his cloak. The Wind was convinced it would win. After all — the wind can fell the strongest tree. The Wind blew and blew with all its strength. The result however was that the traveller simply clung to their cloak all the tighter.

The Sun, who was not expected to win the duel, simply shared it’s warmth. With this gentler approach, the Sun won the bet.

Statements and questions are similar. As leaders and teachers we might think the way to success is with a good strong blast from a good strong statement. Success, insight, and understanding however, more frequently come not from the push of the statement, but from that undervalued pull of a well-placed question.

Click HERE to receive a full copy of The How To Guide on Remote Learning.

Peter Watts is a Senior Instructional Designer and Facilitator. He works on both fassforward's Live, Live/online and tailored programs. Peter is fassforward's lead instructional designer for Live/online experiences which deliver mission-critical leadership and communications training, globally, at scale.

Eugene Yoon is a graphic designer and illustrator at fassforward. She is a crafter of Visual Logic. Eugene is multifaceted and works on various types of projects, including but not limited to product design, UX and web design, data visualization, print design, advertising, and presentation design.

¹ Yan, Veronica X., et al. "Why does guessing incorrectly enhance, rather than impair, retention?" Memory & cognition 42.8 (2014): 1373-1383.
² Ibid.
³ “The Cost of Poor Communications.” SHRM, 30 July 2020.
⁴ “It Doesn’t Hurt to Ask: Question-Asking Encourages Self-Disclosure and Increases Liking” Huang, Yeomans, Wood Brooks, Minson, and Gino. Journal of Personality and Social Psychology 113, no. 3 (September 2017): 430–452.
⁵ Guthridge, Liz. “Council Post: How You Can Benefit By Asking More Questions.” Forbes, 12 Sept. 2017.
⁶ Hoffeld, David. “Want To Know What Your Brain Does When It Hears A Question?” Fast Company, 21 Feb. 2017.
⁷ Hagel, John. “Good Leadership Is About Asking Good Questions.” Harvard Business Review, 8 Jan. 202.
⁸ Einav Hart, Eric VanEpps, Maurice E. Schweitzer. “I Didn’t Want to Offend You: The Cost of Avoiding Sensitive Questions
⁹ Ronald E. Riggio. “The Dangerous Art of Impression Management.” Psychology Today, 25 Oct. 2013.
¹⁰ SuperOkay. “Why Are Humans so Bad at Estimating?” SuperOkay, 11 Oct. 2017.
¹¹ Hart, Einav. “The Case for Asking Sensitive Questions.” Harvard Business Review, 24 Nov. 2020.
¹² Corcuera, Lorie. “5 Mistaken Beliefs About Asking for Help.” Inc., 10 Sept. 2014.
¹³ “The Science of Asking Great Questions.” AMA.
¹⁴ “React vs Respond.” Psychology Today, 1 Sept. 2016.

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